Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Ola F. Wendt'
'Mostafa El Masnaouy'
'Patrik Nilsson'
'Daniel Olsson'

_publ_contact_author_name        'Dr Ola F Wendt'
_publ_contact_author_address     
;
Department of Chemistry
Lund University
PO Box 124
Lund
221-00
SWEDEN
;

_publ_contact_author_email       OLA.WENDT@INORG.LU.SE

_publ_requested_journal          'Dalton Transactions'

_publ_section_title              
;
A catalytic and mechanistic investigation of a PCP
pincer palladium complex in the Stille reaction
;

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 256981'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H35 Cl O P2 Pd'
_chemical_formula_weight         687.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   15.016(2)
_cell_length_b                   15.016(2)
_cell_length_c                   14.129(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3185.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5579
_cell_measurement_theta_min      2.397
_cell_measurement_theta_max      29.474

_exptl_crystal_description       octahedron
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.708525
_exptl_absorpt_correction_T_max  0.881457
_exptl_absorpt_process_details   
'absorption corrections using SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            32386
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         31.67
_reflns_number_total             5069
_reflns_number_gt                3894
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (Brandenburg)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         5069
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.378032(10) 0.378032(10) 0.0000 0.03989(7) Uani 1 2 d S . .
P1 P 0.29764(4) 0.48525(4) 0.07792(4) 0.04303(14) Uani 1 1 d . . .
Cl1 Cl 0.26444(3) 0.26444(3) 0.0000 0.05403(19) Uani 1 2 d S . .
C1 C 0.47399(13) 0.47399(13) 0.0000 0.0466(7) Uani 1 2 d S . .
C2 C 0.46321(16) 0.55218(17) 0.05432(18) 0.0531(6) Uani 1 1 d . . .
C3 C 0.5292(2) 0.6183(2) 0.0523(2) 0.0768(9) Uani 1 1 d . . .
H3 H 0.5211 0.6706 0.0865 0.092 Uiso 1 1 calc R . .
C4 C 0.60632(19) 0.60632(19) 0.0000 0.0881(15) Uani 1 2 d S . .
H4 H 0.6501 0.6501 0.0000 0.106 Uiso 1 2 calc SR . .
C5 C 0.38426(18) 0.56298(18) 0.1169(2) 0.0586(6) Uani 1 1 d . . .
H5A H 0.3623 0.6237 0.1134 0.070 Uiso 1 1 calc R . .
H5B H 0.4006 0.5506 0.1821 0.070 Uiso 1 1 calc R . .
C11 C 0.22032(14) 0.54531(14) 0.00201(17) 0.0458(5) Uani 1 1 d . . .
C12 C 0.17608(19) 0.49825(18) -0.0677(2) 0.0615(7) Uani 1 1 d . . .
H12 H 0.1875 0.4379 -0.0761 0.074 Uiso 1 1 calc R . .
C13 C 0.1142(2) 0.5414(2) -0.1257(2) 0.0779(9) Uani 1 1 d . . .
H13 H 0.0841 0.5091 -0.1719 0.094 Uiso 1 1 calc R . .
C14 C 0.0975(2) 0.6295(3) -0.1158(2) 0.0723(8) Uani 1 1 d . . .
H14 H 0.0563 0.6574 -0.1550 0.087 Uiso 1 1 calc R . .
C15 C 0.1415(3) 0.6775(2) -0.0475(3) 0.0805(10) Uani 1 1 d . . .
H15 H 0.1303 0.7381 -0.0411 0.097 Uiso 1 1 calc R . .
C16 C 0.2027(2) 0.63603(17) 0.0124(2) 0.0637(7) Uani 1 1 d . . .
H16 H 0.2316 0.6688 0.0590 0.076 Uiso 1 1 calc R . .
C21 C 0.23345(17) 0.46009(16) 0.18413(17) 0.0499(5) Uani 1 1 d . . .
C22 C 0.1929(2) 0.5262(2) 0.2362(3) 0.0852(11) Uani 1 1 d . . .
H22 H 0.1967 0.5852 0.2165 0.102 Uiso 1 1 calc R . .
C23 C 0.1463(3) 0.5048(3) 0.3184(3) 0.0938(12) Uani 1 1 d . . .
H23 H 0.1188 0.5497 0.3531 0.113 Uiso 1 1 calc R . .
C24 C 0.1406(2) 0.4197(3) 0.3478(2) 0.0821(10) Uani 1 1 d . . .
H24 H 0.1085 0.4055 0.4020 0.099 Uiso 1 1 calc R . .
C25 C 0.1813(3) 0.3562(3) 0.2986(3) 0.1001(14) Uani 1 1 d . . .
H25 H 0.1778 0.2978 0.3201 0.120 Uiso 1 1 calc R . .
C26 C 0.2286(3) 0.3736(2) 0.2167(2) 0.0813(10) Uani 1 1 d . . .
H26 H 0.2566 0.3277 0.1841 0.098 Uiso 1 1 calc R . .
O1 O 0.6715(5) 0.3285(5) 0.2500 0.303(6) Uani 1 2 d S . .
C31 C 0.5831(5) 0.3214(5) 0.2905(5) 0.159(3) Uani 1 1 d . . .
H31A H 0.5855 0.3255 0.3590 0.190 Uiso 1 1 calc R . .
H31B H 0.5555 0.2653 0.2732 0.190 Uiso 1 1 calc R . .
C32 C 0.5337(4) 0.3967(6) 0.2502(7) 0.207(4) Uani 1 1 d . . .
H32A H 0.4837 0.4134 0.2898 0.248 Uiso 1 1 calc R . .
H32B H 0.5127 0.3837 0.1868 0.248 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd1 0.03749(8) 0.03749(8) 0.04469(11) -0.00125(8) 0.00125(8) -0.00141(10)
P1 0.0442(3) 0.0387(3) 0.0462(3) -0.0042(2) -0.0019(2) 0.0012(2)
Cl1 0.0461(2) 0.0461(2) 0.0698(5) -0.0053(3) 0.0053(3) -0.0078(3)
C1 0.0439(10) 0.0439(10) 0.0519(17) 0.0057(13) -0.0057(13) -0.0091(12)
C2 0.0500(14) 0.0506(14) 0.0588(14) -0.0004(11) -0.0083(11) -0.0106(11)
C3 0.083(2) 0.0628(18) 0.085(2) -0.0070(17) -0.0115(17) -0.0283(17)
C4 0.081(2) 0.081(2) 0.103(4) -0.015(2) 0.015(2) -0.043(3)
C5 0.0549(15) 0.0537(14) 0.0672(15) -0.0178(12) -0.0144(13) -0.0036(12)
C11 0.0467(11) 0.0447(11) 0.0459(11) 0.0003(11) 0.0018(12) 0.0017(9)
C12 0.0636(16) 0.0489(14) 0.0721(18) -0.0075(13) -0.0162(14) 0.0013(12)
C13 0.073(2) 0.089(2) 0.0723(18) -0.0090(16) -0.0242(17) 0.0086(18)
C14 0.0685(18) 0.084(2) 0.0642(17) 0.0143(17) -0.0103(14) 0.0160(17)
C15 0.092(3) 0.0553(17) 0.095(2) 0.0078(17) -0.011(2) 0.0228(17)
C16 0.0771(18) 0.0477(14) 0.0662(17) -0.0035(14) -0.0139(15) 0.0099(12)
C21 0.0548(14) 0.0494(13) 0.0454(12) -0.0003(10) -0.0012(11) 0.0071(11)
C22 0.112(3) 0.0593(17) 0.084(2) 0.0056(17) 0.037(2) 0.0201(17)
C23 0.100(3) 0.099(3) 0.082(2) -0.003(2) 0.035(2) 0.027(2)
C24 0.077(2) 0.109(3) 0.0604(18) 0.0092(18) 0.0175(16) -0.0030(19)
C25 0.153(4) 0.071(2) 0.076(2) 0.0106(19) 0.042(3) -0.004(2)
C26 0.122(3) 0.0558(17) 0.0662(17) 0.0053(15) 0.0267(18) 0.0073(19)
O1 0.229(6) 0.229(6) 0.45(2) 0.008(9) 0.008(9) 0.003(9)
C31 0.162(6) 0.185(7) 0.129(5) 0.026(5) -0.024(4) -0.065(5)
C32 0.112(4) 0.384(12) 0.123(4) 0.009(11) 0.001(5) -0.005(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 2.038(3) . ?
Pd1 P1 2.2938(6) . ?
Pd1 P1 2.2938(6) 7 ?
Pd1 Cl1 2.4123(8) . ?
P1 C11 1.820(2) . ?
P1 C21 1.823(3) . ?
P1 C5 1.832(3) . ?
C1 C2 1.412(3) . ?
C1 C2 1.412(3) 7 ?
C2 C3 1.402(4) . ?
C2 C5 1.488(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C3 1.386(4) 7 ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C12 1.383(4) . ?
C11 C16 1.396(3) . ?
C12 C13 1.399(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C22 1.377(4) . ?
C21 C26 1.380(4) . ?
C22 C23 1.393(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.346(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.329(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O1 C31 1.450(9) 8_665 ?
O1 C31 1.450(9) . ?
C31 C32 1.467(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C32 1.478(14) 8_665 ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Pd1 P1 82.867(16) . . ?
C1 Pd1 P1 82.867(16) . 7 ?
P1 Pd1 P1 165.73(3) . 7 ?
C1 Pd1 Cl1 180.000(11) . . ?
P1 Pd1 Cl1 97.133(16) . . ?
P1 Pd1 Cl1 97.133(16) 7 . ?
C11 P1 C21 104.51(11) . . ?
C11 P1 C5 108.34(12) . . ?
C21 P1 C5 105.04(13) . . ?
C11 P1 Pd1 113.63(8) . . ?
C21 P1 Pd1 121.86(8) . . ?
C5 P1 Pd1 102.59(9) . . ?
C2 C1 C2 119.1(3) . 7 ?
C2 C1 Pd1 120.46(14) . . ?
C2 C1 Pd1 120.46(14) 7 . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 C5 119.8(2) . . ?
C1 C2 C5 120.3(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C3 120.0(4) 7 . ?
C3 C4 H4 120.0 7 . ?
C3 C4 H4 120.0 . . ?
C2 C5 P1 108.49(17) . . ?
C2 C5 H5A 110.0 . . ?
P1 C5 H5A 110.0 . . ?
C2 C5 H5B 110.0 . . ?
P1 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 P1 118.25(18) . . ?
C16 C11 P1 122.89(19) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.8(3) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C22 C21 C26 118.5(3) . . ?
C22 C21 P1 121.6(2) . . ?
C26 C21 P1 119.9(2) . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 122.6(4) . . ?
C24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C21 C26 C25 119.0(3) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C31 O1 C31 106.9(9) 8_665 . ?
O1 C31 C32 104.7(6) . . ?
O1 C31 H31A 110.8 . . ?
C32 C31 H31A 110.8 . . ?
O1 C31 H31B 110.8 . . ?
C32 C31 H31B 110.8 . . ?
H31A C31 H31B 108.9 . . ?
C31 C32 C32 100.9(5) . 8_665 ?
C31 C32 H32A 111.6 . . ?
C32 C32 H32A 111.6 8_665 . ?
C31 C32 H32B 111.6 . . ?
C32 C32 H32B 111.6 8_665 . ?
H32A C32 H32B 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        31.67
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.050